feat(uploads): write prompt uploads to a hidden, self-ignoring .codeman-uploads/ folder

A pasted image landed in <workspace>/.claude-images/, a name that belongs to another tool, in a folder nothing ignored, so it showed up in git status of every case that ever received a paste. Uploads now go to a flat <workspace>/.codeman-uploads/ that carries a .gitignore of `*` (written once, never over a file already there): in the workspace because that is the only path identical for a local agent and a container, flat because a nested .codeman/ is the data dir itself when the workspace is the home directory.

The directory names live in paste-image-gc.ts alone. The old folder receives nothing but stays readable for one release: the hourly sweep and the delete cleanup go through uploadDirs(), the image watcher's ignore filter reads the names. uploadDirs() lists only real directories, none that is, contains or sits inside the data dir, and nothing for a remote session, since both consumers delete. The route refuses a remote (SSH) session before touching disk: the file would land on this host under the remote path, where the agent cannot read it.

test/paste-image-dir-shared.test.ts binds port 0 and leaves the port guard's legacy list.

Decided in #553.

.gitignore

@@ -107,7 +107,9 @@ todo.md
 @fix_plan.md
 readme-preview.mjs
 
-# Uploaded images land here under each session working dir (runtime artifact)
+# Prompt uploads land here under each session working dir (runtime artifact);
+# .claude-images/ is where they landed before the move.
+.codeman-uploads/
 .claude-images/
 
 # Local-LLM harness smoke-test config (real IPs/keys) — see the .example.json

docs/api-reference.md

@@ -466,6 +466,21 @@ geometry was read. The capture runs synchronous tmux calls on the server; the
 | `tail=<bytes>` | Keep the newest `<bytes>` of the result (`truncationReason: 'tail'` when it cut). |
 | `lines=<n>` | With `full=1` only: read at most `<n>` lines of tmux history above the visible frame. An integer of at least 1, clamped to the configured history limit; absent or malformed, the whole limit (100,000 lines by default), as before. `truncated` and `truncationReason` describe byte cuts only, not this bound. Without it a full capture reads all of that history before `tail` cuts it, so a client that keeps a fixed number of lines (the tile grid sends its xterm's scrollback plus its rows) should send it. |
 
+## Prompt uploads (`POST /api/v1/sessions/:id/paste-image`)
+
+A `multipart/form-data` body with one `image` part. The file is written into the
+session's workspace as `<workingDir>/.codeman-uploads/paste-<ms>-<hex>.<ext>`, and
+`data` carries `path` and `filename` for the client to type the path into the
+prompt. The folder is Codeman's own: hidden, created on first use with a
+`.gitignore` containing `*` (written once, never over a file already there), and
+cleaned up the way pasted images always were: `paste-*` files older than 7 days
+go in an hourly sweep, and the folder goes when the last session of that
+workspace is killed. Uploads made before this release sit in `.claude-images/`;
+that folder receives nothing new, and is swept and removed the same way for one
+release. A remote (SSH) session answers 400, since the file would land on the
+Codeman host under a path the remote agent cannot read; Docker sessions are
+fine, their workspace is bind-mounted at the same absolute path.
+
 ## Session lineage (`parentSessionId`)
 
 A create request may name the session that spawned it, which the web UI draws as a

docs/architecture-invariants.md

@@ -254,7 +254,7 @@ Further detail, closing: ⚠️ **Closing has the mirror-image race and one owne
 - **No start, attach or relaunch may be in flight** (`Session.paneLifecycleInFlight`, raised for the whole of `_setupOrAttachMuxSession()` and `restartCli()`). The dead-pane respawn revives an exited pane on purpose, and the pane reads as dead until `clearPaneExitForNewPane()` runs after its startup delay.
 - **The pane must have been up for `CLEAN_EXIT_MIN_PANE_LIFETIME_MS` (10 s)** since the last start, attach or relaunch finished (`Session.paneStartedAt`). A CLI that prints a startup error and exits 0 would otherwise lose its tab, and the error with it, seconds after launch; its row stays as `exited (0)` instead. An attach to an already running pane stamps it too, so an `/exit` within seconds of a server restart leaves a row to close by hand.
 
-Scoping needs no check of its own here: `setPaneExit()` already forces `paneExit` to UNKNOWN for direct-PTY, remote, docker and discovered sessions. There is no setting, by the maintainer's decision on #446. ⚠️ Do not flip local panes to `remain-on-exit failed` to get the same effect: a destroyed pane ends the tmux session, the PTY exit nulls the pid, and the browser's `selectSession()` then launches a fresh CLI. `cleanupSession()` keeps `{workingDir}/.claude-images` while another session still uses that directory (`pasteImageDirInUseByOtherSession()`, `paste-image-gc.ts`), since the sweep would otherwise routinely delete a live sibling's pasted images. Paths are compared by `realpath`, and a detached session counts through its persisted record, because `killMux=false` removes it from the map while its pane keeps running; only a session being KILLED is exempt. Each exit gets ONE close attempt (keyed by session id and `at`), and a session being closed refuses `startInteractive()`/`startShell()` (`Session.markClosing()`), so a start that races the close cannot orphan a tmux session. `planRebootRestore()` refuses a record whose persisted `paneExit` is clean (`agent-exited`), which covers an agent that exited just before the power went, before the sweep reached it. Tests: `test/pane-exit-sweep.test.ts`, `test/paste-image-dir-shared.test.ts`, `test/reboot-restore.test.ts`, `test/tmux-manager.test.ts`.
+Scoping needs no check of its own here: `setPaneExit()` already forces `paneExit` to UNKNOWN for direct-PTY, remote, docker and discovered sessions. There is no setting, by the maintainer's decision on #446. ⚠️ Do not flip local panes to `remain-on-exit failed` to get the same effect: a destroyed pane ends the tmux session, the PTY exit nulls the pid, and the browser's `selectSession()` then launches a fresh CLI. `cleanupSession()` keeps `{workingDir}/.codeman-uploads` (and the pre-move `.claude-images`) while another session still uses that directory (`pasteImageDirInUseByOtherSession()`, `paste-image-gc.ts`), since the sweep would otherwise routinely delete a live sibling's pasted images. Paths are compared by `realpath`, and a detached session counts through its persisted record, because `killMux=false` removes it from the map while its pane keeps running; only a session being KILLED is exempt. Each exit gets ONE close attempt (keyed by session id and `at`), and a session being closed refuses `startInteractive()`/`startShell()` (`Session.markClosing()`), so a start that races the close cannot orphan a tmux session. `planRebootRestore()` refuses a record whose persisted `paneExit` is clean (`agent-exited`), which covers an agent that exited just before the power went, before the sweep reached it. Tests: `test/pane-exit-sweep.test.ts`, `test/paste-image-dir-shared.test.ts`, `test/reboot-restore.test.ts`, `test/tmux-manager.test.ts`.
 
 ### Dead-pane respawn: the resume pin
 
@@ -351,7 +351,7 @@ The escape hatch is the synced `workspaceHooksEnabled` setting (App Settings →
 
 ⚠️ Claude-mode only (others carry their conversation id in their own config object), and remote/docker sessions are never offered (`remote-or-docker`), because both need another host or container to be up.
 
-⚠️ A failed rebuild is undone with `discardPartiallyBuiltSession()`, deliberately NOT `cleanupSession()`: the delete path would count the session's tokens into the lifetime totals, demote a pinned record to `stopped` (which this pass reads as an intentional kill, making the session permanently unrestorable) and recursively remove the WORKSPACE's `.claude-images`.
+⚠️ A failed rebuild is undone with `discardPartiallyBuiltSession()`, deliberately NOT `cleanupSession()`: the delete path would count the session's tokens into the lifetime totals, demote a pinned record to `stopped` (which this pass reads as an intentional kill, making the session permanently unrestorable) and recursively remove the WORKSPACE's upload dirs (`.codeman-uploads`, and the pre-move `.claude-images`).
 
 ⚠️ `os.uptime()` reports the HOST's uptime, which a container shares, and that cuts both ways: after a genuine host reboot a containerized Codeman does see a short uptime and the banner works, but a container-only restart is invisible to it, which is the case where this would help most. Tests: `test/reboot-restore.test.ts`, `test/routes/reboot-restore-routes.test.ts`, `test/routes/reboot-restore-rebuild-failure.test.ts`, `test/discard-partially-built-session.test.ts`.
 
@@ -1063,6 +1063,8 @@ Tests: `test/mobile-prompt-composer.test.ts` (in the CI gate, deliberately not u
 
 Target: 20 sessions, 50 agent windows at 60fps. Limits in `src/config/`: terminal 32MB (see below), text 1MB, messages 1000, max agents 500, max sessions 50, max SSE clients 100. **Terminal history** (`src/config/terminal-history.ts`, COD-80): tmux history-limit 100k lines, PTY buffer 32MB max / 24MB trim (env `CODEMAN_MAX_TERMINAL_BUFFER`/`CODEMAN_TRIM_TERMINAL_TO`; the env-derived trim is clamped ≤75% of max — trim ≥ max would disable `BufferAccumulator` trimming entirely = unbounded memory); browser xterm scrollback stays a separate hardcoded 50k (`DEFAULT_SCROLLBACK` in constants.js — 100k/tab is a mobile-memory hazard). tmux <3.7 allocates history at pane creation, so `createSession()` sets the global default in the same command queue immediately before `new-session`; tmux 3.7+ instead creates the session and targets only that pane, because changing the global option can resize and trim unrelated live panes. A settings change resizes tracked panes only on 3.7+ and otherwise affects future panes; no version can recover lines already evicted. Settings keys `terminalScrollbackLines`/`terminalBufferMaxBytes`/`terminalBufferTrimBytes` are schema-validated but inert (only `tmuxHistoryLimit` is wired); `buffer-limits.ts` re-exports the defaults. Text/message limits are env-overridable too (`CODEMAN_MAX_TEXT_OUTPUT`/`CODEMAN_TRIM_TEXT_TO`/`CODEMAN_MAX_MESSAGES`). **Image upload** (`image-input.js` / `config/buffer-limits.ts`): up to `_maxBatchImages` 20 images/batch (bounded concurrency 3), per-file `MAX_PASTE_IMAGE_BYTES` 50MB (env `CODEMAN_MAX_PASTE_IMAGE_BYTES`); the mobile camera-roll picker auto-downscales to fit before upload. **HEIC paste uploads** (#151): converted server-side to JPEG in a `worker_threads` worker (`web/heic-jpeg-worker.ts`, resourceLimits + 30s timeout) gated by `runWithConversionLimit()`; detection is magic-byte based (covers Android/MIUI HEIFs mislabeled as JPEG); headers declaring > 64MP are rejected 415 BEFORE decode (decompression-bomb guard). Deps: `heic-decode` + `jpeg-js`. Use `LRUMap` for bounded caches, `StaleExpirationMap` for TTL cleanup. Anti-flicker pipeline: `docs/terminal-anti-flicker.md`.
 
+**Prompt uploads live in `<workspace>/.codeman-uploads/`** (`POST /api/sessions/:id/paste-image`; the names live ONLY in `src/web/paste-image-gc.ts`): IN the workspace because that is the only path that resolves identically for a local agent and a container (only the workspace is bind-mounted, at the same absolute path; `~/.codeman` is not); hidden so it stays out of `git status` and the agent's view of the repository; FLAT because a nested `<workspace>/.codeman/` IS the data dir (`join(homedir(), '.codeman')`, `src/config/instance.ts`) when the workspace is the home directory, which nothing refuses; and self-ignoring through a `.gitignore` of `*` written once with `wx`, so a file already there is the user's and stays. The pre-move `.claude-images/` receives nothing but stays readable for one release: `UPLOAD_DIR_NAMES` lists both, the hourly sweep and the delete cleanup in `cleanupSession()` go through `uploadDirs()`, and the image watcher's ignore filter reads the names. ⚠️ `uploadDirs()` returns only REAL directories (lstat at the leaf, so a planted `.codeman-uploads -> /other-case/.codeman-uploads` is never listed: `readdir` follows a link to a directory, and the sweep would otherwise age out the other case's uploads through it), none that is, contains or sits inside `getDataDir()` (contrived, `CODEMAN_INSTANCE=uploads` makes `~/.codeman-uploads` the data dir of a home workspace and `CODEMAN_DATA_DIR` can point inside one, but it is one check next to a recursive delete), and nothing for a remote (SSH) session, whose `workingDir` is the remote path and would otherwise name a same-named LOCAL directory for the sweep and the delete. The check is made when the directories are listed: a same-user process that swaps a listed directory for a link during the sweep's awaits is accepted (Node has no `openat()`, and that actor already writes anywhere this process can). The route refuses a remote (SSH) session with 400 before any disk touch: its `workingDir` is the remote path, so the file would land on THIS host where the agent cannot read it. Tests: `test/paste-image-gc.test.ts`, `test/paste-image-dir-shared.test.ts`, the paste-image block of `test/routes/session-routes.test.ts`.
+
 ### Process-tree walks are bounded
 
 **Process-tree walks are bounded** (`proc-tree.ts`, pure + unit tested): `collectDescendants(pid, byParent)` is the ONE descendant traversal, fed by a single cached `ps -eo pid=,ppid=` snapshot (`refreshProcSnapshot()` in tmux-manager.ts: in-flight-shared, async because `execSync`'s timeout cannot return at all while spawnSync waits on an unkillable child, and ANY error discards the result rather than caching a truncated `ps`, which would make whole subtrees invisible to the kill path).

src/image-watcher.ts

@@ -14,6 +14,7 @@ import { basename, extname, relative } from 'node:path';
 import { statSync } from 'node:fs';
 import type { AttachmentDetectedEvent, AttachmentDetectedType, ImageDetectedEvent } from './types.js';
 import { KeyedDebouncer } from './utils/index.js';
+import { UPLOAD_DIR_NAMES } from './web/paste-image-gc.js';
 
 // ========== Types ==========
 
@@ -157,12 +158,15 @@ export class ImageWatcher extends EventEmitter {
         // Watch all subdirectories (images may be saved in src/, assets/, etc.)
         // Ignore common heavy directories for performance
         ignored: (path: string) => {
-          // Skip node_modules, .git, and other heavy directories
+          // Skip node_modules, .git, and other heavy directories, and Codeman's
+          // own upload folders: a pdf the user handed to the agent is not a file
+          // the agent produced.
           if (
             path.includes('/node_modules/') ||
             path.includes('/.git/') ||
             path.includes('/dist/') ||
-            path.includes('/.next/')
+            path.includes('/.next/') ||
+            UPLOAD_DIR_NAMES.some((name) => path.includes(`/${name}/`))
           ) {
             return true;
           }

src/web/paste-image-gc.ts

@@ -1,25 +1,76 @@
 /**
- * @fileoverview Periodic GC for paste-image files.
+ * @fileoverview Periodic GC for prompt-upload files, and the one place that
+ * names the directories they live in.
  *
  * Without cleanup, /api/sessions/:id/paste-image accumulates files indefinitely
- * under {workingDir}/.claude-images/. The route only triggers cleanup on
+ * under {workingDir}/.codeman-uploads/. The route only triggers cleanup on
  * killMux=true session deletion, so long-lived sessions can fill disk under
  * heavy pasting. This sweeper bounds disk use by deleting `paste-*` files
- * older than MAX_AGE_MS from each live session's image dir on an interval.
+ * older than MAX_AGE_MS from each live session's upload dirs on an interval.
  *
  * Conservative defaults — only files matching the `paste-` prefix are
  * considered, and we lstat (not stat) so a planted symlink cannot escape the
- * image dir.
+ * upload dir.
  */
 import fs from 'node:fs/promises';
-import { realpathSync } from 'node:fs';
-import { join, resolve } from 'node:path';
+import { lstatSync, realpathSync } from 'node:fs';
+import { join, resolve, sep } from 'node:path';
+import { getDataDir } from '../config/instance.js';
 import type { SessionPort } from './ports/index.js';
 
 const MAX_AGE_MS = 7 * 24 * 60 * 60 * 1000; // 7 days
 const SWEEP_INTERVAL_MS = 60 * 60 * 1000; // 1 hour
 const INITIAL_DELAY_MS = 30 * 1000; // 30s after startup
 
+/**
+ * Where a prompt upload is written, relative to the session's working
+ * directory. IN the workspace, because that is the only path that resolves
+ * identically for a local agent and a container (only the workspace is
+ * bind-mounted, at the same absolute path); hidden, so it stays out of
+ * `git status` and the agent's view of the repository; FLAT, because a nested
+ * `<workspace>/.codeman/` is Codeman's own data dir when the workspace is the
+ * home directory; and self-ignoring, through a `.gitignore` of `*` the route
+ * writes once.
+ */
+export const UPLOADS_DIR = '.codeman-uploads';
+/** Where uploads landed before the move: written to by nothing, readable for one release. */
+export const LEGACY_UPLOADS_DIR = '.claude-images';
+/** Every upload dir name, current first. Retiring the legacy one here retires it for every reader. */
+export const UPLOAD_DIR_NAMES = [UPLOADS_DIR, LEGACY_UPLOADS_DIR];
+
+/**
+ * Every directory a session's uploads sit in, current first. Both consumers
+ * act on what this returns, the hourly sweep and the recursive delete in
+ * cleanupSession(), so it lists only REAL directories (a link planted by a
+ * workspace script, `.codeman-uploads -> /other-case/.codeman-uploads`, is
+ * not one; readdir follows a link to a directory), none that is, contains or
+ * sits inside this instance's data dir (a home workspace reaches it under a
+ * contrived instance name, `CODEMAN_INSTANCE=uploads`, and `CODEMAN_DATA_DIR`
+ * can point inside one), and nothing for a remote (SSH) session, whose
+ * workingDir is the remote path and would name a same-named LOCAL directory
+ * here. The check is made when listing: a same-user process that swaps a
+ * listed directory for a link afterwards is accepted, since it already writes
+ * anywhere this process can.
+ */
+export function uploadDirs(session: { workingDir: string; remote?: unknown }): string[] {
+  if (session.remote) return [];
+  const dataDir = canonicalDir(getDataDir());
+  return UPLOAD_DIR_NAMES.map((name) => join(session.workingDir, name)).filter((dir) => {
+    if (!isRealDir(dir)) return false;
+    const real = canonicalDir(dir);
+    return real !== dataDir && !real.startsWith(dataDir + sep) && !dataDir.startsWith(real + sep);
+  });
+}
+
+/** lstat, so a symlink is not a directory, whatever it points at. */
+function isRealDir(p: string): boolean {
+  try {
+    return lstatSync(p).isDirectory();
+  } catch {
+    return false;
+  }
+}
+
 export async function sweepPasteImagesOnce(
   ctx: Pick<SessionPort, 'sessions'>,
   now: number = Date.now()
@@ -28,26 +79,27 @@ export async function sweepPasteImagesOnce(
   let scanned = 0;
   let deleted = 0;
   for (const session of ctx.sessions.values()) {
-    const dir = join(session.workingDir, '.claude-images');
-    let entries: string[];
-    try {
-      entries = await fs.readdir(dir);
-    } catch {
-      continue; // dir absent — nothing to do
-    }
-    for (const name of entries) {
-      if (!name.startsWith('paste-')) continue;
-      const p = join(dir, name);
-      scanned += 1;
+    for (const dir of uploadDirs(session)) {
+      let entries: string[];
       try {
-        const st = await fs.lstat(p);
-        if (!st.isFile()) continue;
-        if (st.mtimeMs < cutoff) {
-          await fs.unlink(p);
-          deleted += 1;
-        }
+        entries = await fs.readdir(dir);
       } catch {
-        // best-effort: skip permission/race errors silently
+        continue; // gone since listed — nothing to do
+      }
+      for (const name of entries) {
+        if (!name.startsWith('paste-')) continue;
+        const p = join(dir, name);
+        scanned += 1;
+        try {
+          const st = await fs.lstat(p);
+          if (!st.isFile()) continue;
+          if (st.mtimeMs < cutoff) {
+            await fs.unlink(p);
+            deleted += 1;
+          }
+        } catch {
+          // best-effort: skip permission/race errors silently
+        }
       }
     }
   }
@@ -55,7 +107,7 @@ export async function sweepPasteImagesOnce(
 }
 
 /**
- * The path two sessions must share to share a paste-image dir: the canonical
+ * The path two sessions must share to share an upload dir: the canonical
  * path when it can be resolved, so a sibling that reaches the same directory
  * through a symlink matches, and the normalised path otherwise (a directory
  * that no longer exists has nothing left to protect).
@@ -68,7 +120,7 @@ function canonicalDir(dir: string): string {
   }
 }
 
-/** One session the paste-image guard weighs: its id, directory and, for a persisted record, its status. */
+/** One session the upload-dir guard weighs: its id, directory and, for a persisted record, its status. */
 export interface PasteImageDirUser {
   id: string;
   workingDir: string;
@@ -76,11 +128,11 @@ export interface PasteImageDirUser {
 }
 
 /**
- * Does another live session still use this working directory's paste-image
- * dir? Deleting a session removes `{workingDir}/.claude-images` recursively,
- * and several sessions routinely share one case directory, so without this
- * check closing one session deletes the pasted images a sibling in the same
- * case still refers to.
+ * Does another live session still use this working directory's upload dirs?
+ * Deleting a session removes them (`uploadDirs()`) recursively, and several
+ * sessions routinely share one case directory, so without this check closing
+ * one session deletes the pasted images a sibling in the same case still
+ * refers to.
  *
  * Two kinds of sibling count as live:
  *

src/web/public/terminal-ui.js

@@ -2004,7 +2004,7 @@ Object.assign(CodemanApp.prototype, {
         const cmdPattern = /\b(tail|cat|head|less|grep|watch|vim|nano)\s+(?:[^\s\/]+\s+){0,4}(\/[^\s"'<>|;&\n\x00-\x1f]+)/g;
 
         // Pattern 2: Paths with common extensions. Image/PDF/media extensions are
-        // included so pasted-attachment paths (`.claude-images/paste-*.png`) and
+        // included so pasted-attachment paths (`.codeman-uploads/paste-*.png`) and
         // screenshots an agent just wrote are clickable; those open the file
         // preview rather than the log viewer (see addLink).
         //

src/web/routes/reboot-restore-routes.ts

@@ -275,7 +275,7 @@ export function registerRebootRestoreRoutes(app: FastifyInstance, ctx: RebootRes
           // count this session's historical tokens into the lifetime totals, demote
           // a pinned record to `stopped` (which this pass reads as an intentional
           // kill, making the session permanently unrestorable) and delete the
-          // workspace's `.claude-images`. This undoes only the construction.
+          // workspace's `.codeman-uploads`. This undoes only the construction.
           await ctx
             .discardPartiallyBuiltSession(entry.sessionId)
             .catch((discardErr: unknown) =>

src/web/routes/session-routes.ts

@@ -188,6 +188,7 @@ import {
 } from '../response-viewer-transcript.js';
 import { readDeepSeekLastResponse } from '../../deepseek-transcript.js';
 import { appendClaudeCustomTitle } from '../../claude-session-title.js';
+import { UPLOADS_DIR } from '../paste-image-gc.js';
 
 // Path to linked-cases registry (same file used by case-routes resolveCasePath)
 const LINKED_CASES_FILE = dataPath('linked-cases.json');
@@ -361,6 +362,50 @@ export function imageMagicMatchesExt(data: Buffer, ext: string): boolean {
   }
 }
 
+/**
+ * Create or re-verify `{workingDir}/.codeman-uploads` for a prompt upload, or
+ * null when something other than a regular directory sits there. An agent or
+ * postinstall script could plant `.codeman-uploads -> ~/.ssh/` and redirect
+ * future writes outside workingDir: lstat (not stat) sees the symlink itself,
+ * and mkdir without `recursive` does not follow one for the leaf either;
+ * O_EXCL|O_NOFOLLOW on the file open makes the write itself symlink-safe.
+ * The folder ignores itself: a `.gitignore` of `*`, written once with O_EXCL,
+ * so the user's repository never sees uploads, their own ignore file is never
+ * touched, and a file already there is theirs and stays as it is.
+ */
+async function ensureUploadDir(workingDir: string): Promise<string | null> {
+  // workingDir is guaranteed to exist (live session).
+  const uploadDir = join(workingDir, UPLOADS_DIR);
+  try {
+    const dirStat = await fs.lstat(uploadDir);
+    if (dirStat.isSymbolicLink() || !dirStat.isDirectory()) return null;
+  } catch (err: unknown) {
+    if ((err as NodeJS.ErrnoException).code !== 'ENOENT') throw err;
+    try {
+      await fs.mkdir(uploadDir);
+    } catch (mkErr: unknown) {
+      // Concurrent uploads (a batch of photos) race to create the dir — the
+      // losers get EEXIST. Treat an already-present REAL directory as success,
+      // but re-verify it isn't a symlink a racing actor planted.
+      if ((mkErr as NodeJS.ErrnoException).code !== 'EEXIST') throw mkErr;
+      const raceStat = await fs.lstat(uploadDir);
+      if (raceStat.isSymbolicLink() || !raceStat.isDirectory()) return null;
+    }
+  }
+  const ignoreFile = join(uploadDir, '.gitignore');
+  try {
+    // 'wx' = O_CREAT|O_EXCL, which also fails on a symlink at the path.
+    await fs.writeFile(ignoreFile, '*\n', { flag: 'wx' });
+  } catch (err: unknown) {
+    if ((err as NodeJS.ErrnoException).code === 'EEXIST') return uploadDir;
+    // The create can succeed before the write fails (ENOSPC): an empty ignore
+    // file would read as the user's on the next upload, so take it back.
+    await fs.rm(ignoreFile, { force: true });
+    throw err;
+  }
+  return uploadDir;
+}
+
 // Per-(IP, sessionId) token bucket for paste-image. 30 requests/minute.
 // Bucket map entries are pruned when they drift > 1h stale to bound memory
 // against a flood of unique IP keys.
@@ -5198,6 +5243,18 @@ export function registerSessionRoutes(
 
     const session = findSessionOrFail(ctx, id, req);
 
+    // The file lands on THIS host under the session's working directory, which
+    // for a remote (SSH) session is the remote path: the agent there could never
+    // read it, and the write would land in a same-named local directory or fail.
+    // Docker is fine, its workspace is bind-mounted at the same absolute path.
+    if (session.remote) {
+      reply.code(400);
+      return createErrorResponse(
+        ApiErrorCode.INVALID_INPUT,
+        'Prompt uploads are not supported for remote (SSH) sessions'
+      );
+    }
+
     if (!req.isMultipart()) {
       reply.code(400);
       return createErrorResponse(ApiErrorCode.INVALID_INPUT, 'Expected multipart/form-data');
@@ -5294,37 +5351,11 @@ export function registerSessionRoutes(
       return createErrorResponse(ApiErrorCode.INVALID_INPUT, `Image bytes do not match declared type ${ext}`);
     }
 
-    // Save to {workingDir}/.claude-images/
-    // Refuse symlinks at imageDir — an agent or postinstall script could plant
-    // `.claude-images -> ~/.ssh/` and redirect future writes outside workingDir.
-    // We lstat (not stat) so we see the symlink itself. Use mkdir without
-    // `recursive` so the leaf creation does not follow a symlink either, and
-    // O_EXCL|O_NOFOLLOW on the file open so the write itself is symlink-safe.
-    const imageDir = join(session.workingDir, '.claude-images');
-    try {
-      const dirStat = await fs.lstat(imageDir);
-      if (dirStat.isSymbolicLink() || !dirStat.isDirectory()) {
-        reply.code(403);
-        return createErrorResponse(ApiErrorCode.INVALID_INPUT, '.claude-images is not a regular directory');
-      }
-    } catch (err: unknown) {
-      if ((err as NodeJS.ErrnoException).code !== 'ENOENT') throw err;
-      // Non-recursive mkdir: does not follow symlinks for the leaf.
-      // session.workingDir is guaranteed to exist (live session).
-      try {
-        await fs.mkdir(imageDir);
-      } catch (mkErr: unknown) {
-        // Concurrent uploads (a batch of photos) race to create .claude-images —
-        // the losers get EEXIST. Treat an already-present REAL directory as
-        // success, but re-verify it isn't a symlink a racing actor planted
-        // (preserve the symlink-safety guarantee above).
-        if ((mkErr as NodeJS.ErrnoException).code !== 'EEXIST') throw mkErr;
-        const raceStat = await fs.lstat(imageDir);
-        if (raceStat.isSymbolicLink() || !raceStat.isDirectory()) {
-          reply.code(403);
-          return createErrorResponse(ApiErrorCode.INVALID_INPUT, '.claude-images is not a regular directory');
-        }
-      }
+    // {workingDir}/.codeman-uploads/, see ensureUploadDir.
+    const imageDir = await ensureUploadDir(session.workingDir);
+    if (!imageDir) {
+      reply.code(403);
+      return createErrorResponse(ApiErrorCode.INVALID_INPUT, `${UPLOADS_DIR} is not a regular directory`);
     }
     // Date.now() collides on same-ms uploads from two tabs (last-write wins
     // silently). Append 8 hex chars so concurrent pastes get distinct names.

src/web/server.ts

@@ -33,7 +33,7 @@ import fastifyCookie from '@fastify/cookie';
 import fastifyStatic from '@fastify/static';
 import fastifyWebsocket from '@fastify/websocket';
 import fastifyMultipart from '@fastify/multipart';
-import { pasteImageDirInUseByOtherSession, startPasteImageGc } from './paste-image-gc.js';
+import { pasteImageDirInUseByOtherSession, startPasteImageGc, uploadDirs } from './paste-image-gc.js';
 import { CLEAN_EXIT_CLOSE_REASON, shouldCloseCleanlyExitedSession } from '../pane-exit-sweep.js';
 import { join, dirname } from 'node:path';
 import { fileURLToPath } from 'node:url';
@@ -1546,11 +1546,14 @@ export class WebServer extends EventEmitter {
           killing: this.killingSessions,
         })
       ) {
-        const pasteImageDir = join(session.workingDir, '.claude-images');
-        try {
-          rmSync(pasteImageDir, { recursive: true, force: true });
-        } catch {
-          // Best-effort cleanup
+        // Both upload dirs, the pre-move one too; uploadDirs() lists only real
+        // directories clear of the data dir, and none for a remote session.
+        for (const uploadDir of uploadDirs(session)) {
+          try {
+            rmSync(uploadDir, { recursive: true, force: true });
+          } catch {
+            // Best-effort cleanup
+          }
         }
       }
       // Drop the agent skill's preamble cache for this session (seeded at create).
@@ -2911,7 +2914,7 @@ export class WebServer extends EventEmitter {
     }
 
     // Bound disk use under heavy paste-image traffic: delete `paste-*` files
-    // older than 7 days from each live session's .claude-images/ hourly.
+    // older than 7 days from each live session's upload dirs hourly.
     if (!this.testMode) {
       this._pasteImageGcStop = startPasteImageGc({ sessions: this.sessions });
       // Surface event-loop stalls (e.g. a slow synchronous tmux/ps call) so the
@@ -3363,7 +3366,7 @@ export class WebServer extends EventEmitter {
    * path adds the session's token totals to the lifetime figures, demotes a
    * pinned record to `stopped` (the durable marker of an intentional kill, which
    * would make the session permanently ineligible for a reboot restore), drops
-   * the persisted Ralph state, and recursively removes `.claude-images` from the
+   * the persisted Ralph state, and recursively removes the upload dirs from the
    * WORKING DIRECTORY, which belongs to the workspace rather than to this session
    * and may hold another live session's pasted images.
    *

test/image-watcher.test.ts

@@ -31,6 +31,7 @@ vi.mock('node:fs', async (importOriginal) => {
 });
 
 import { ImageWatcher } from '../src/image-watcher.js';
+import { watch } from 'chokidar';
 import { statSync } from 'node:fs';
 
 describe('ImageWatcher', () => {
@@ -92,6 +93,14 @@ describe('ImageWatcher', () => {
       expect(watcher.getWatchedSessions()).toHaveLength(1);
     });
 
+    it("ignores Codeman's own upload folders, so a pdf the user handed over is not a detected artifact", () => {
+      watcher.watchSession('session-1', '/home/user/project');
+      const [, opts] = vi.mocked(watch).mock.calls.at(-1) as unknown as [string, { ignored: (p: string) => boolean }];
+      expect(opts.ignored('/home/user/project/.codeman-uploads/paste-1-ab.pdf')).toBe(true);
+      expect(opts.ignored('/home/user/project/.claude-images/paste-1-ab.png')).toBe(true);
+      expect(opts.ignored('/home/user/project/docs/report.pdf')).toBe(false);
+    });
+
     it('should replace watcher when working directory changes', () => {
       watcher.watchSession('session-1', '/home/user/project-a');
       watcher.watchSession('session-1', '/home/user/project-b');

test/link-provider-regex.test.ts

@@ -124,11 +124,11 @@ describe('terminal link-provider regexes (shipped source)', () => {
   });
 
   it('the file-path pattern links pasted image/PDF/media attachment paths', () => {
-    // `.claude-images/paste-*.png` is what Codeman writes for a pasted screenshot;
+    // `.codeman-uploads/paste-*.png` is what Codeman writes for a pasted screenshot;
     // without image extensions the path rendered as plain, unclickable text.
     const ext = shippedPattern('FILE_PATH_LINK_PATTERN');
     const cases = [
-      '/home/arkon/default/claudeman/.claude-images/paste-1785164958410-d11eb7d0.png',
+      '/home/arkon/default/claudeman/.codeman-uploads/paste-1785164958410-d11eb7d0.png',
       '/tmp/shot.jpeg',
       '/opt/app/report.pdf',
       '/home/a/diagram.svg',

test/paste-image-dir-shared.test.ts

@@ -1,8 +1,9 @@
 /**
- * @fileoverview Deleting a session keeps `.claude-images` while a sibling in the
+ * @fileoverview Deleting a session keeps the upload dirs while a sibling in the
  * same working directory is still live (Ark0N/Codeman#446).
  *
- * `cleanupSession()` removes `{workingDir}/.claude-images` recursively. That
+ * `cleanupSession()` removes `{workingDir}/.codeman-uploads` (and the pre-move
+ * `.claude-images`) recursively. That
  * dir belongs to the working directory, not to the session, and several
  * sessions routinely share one case directory, so closing one used to delete
  * the pasted images a live sibling still referred to. The exited-agent sweep
@@ -11,15 +12,13 @@
  *
  * Port: 3188
  */
-import { existsSync, mkdirSync, mkdtempSync, rmSync, symlinkSync, writeFileSync } from 'node:fs';
+import { existsSync, lstatSync, mkdirSync, mkdtempSync, rmSync, symlinkSync, writeFileSync } from 'node:fs';
 import { tmpdir } from 'node:os';
 import { join } from 'node:path';
 import { afterAll, beforeAll, describe, expect, it, vi } from 'vitest';
 import { WebServer } from '../src/web/server.js';
 import { pasteImageDirInUseByOtherSession } from '../src/web/paste-image-gc.js';
 
-const PORT = 3188;
-
 describe('pasteImageDirInUseByOtherSession', () => {
   const none = new Set<string>();
   const check = (
@@ -108,12 +107,13 @@ describe('pasteImageDirInUseByOtherSession', () => {
 describe('deleting a session that shares its working directory', () => {
   let server: WebServer;
   let workingDir: string;
-  const base = `http://localhost:${PORT}`;
+  let base = '';
 
   beforeAll(async () => {
     workingDir = mkdtempSync(join(tmpdir(), 'codeman-paste-shared-'));
-    server = new WebServer(PORT, false, true);
+    server = new WebServer(0, false, true);
     await server.start();
+    base = `http://localhost:${server.boundPort}`;
   });
 
   afterAll(async () => {
@@ -133,18 +133,43 @@ describe('deleting a session that shares its working directory', () => {
 
   const remove = (id: string) => fetch(`${base}/api/sessions/${id}`, { method: 'DELETE' });
 
-  it('keeps the images while a sibling is live, and removes them with the last session', async () => {
+  it('keeps the uploads while a sibling is live, and removes them with the last session', async () => {
     const first = await create();
     const second = await create();
-    const imageDir = join(workingDir, '.claude-images');
-    mkdirSync(imageDir, { recursive: true });
-    writeFileSync(join(imageDir, 'paste-1.png'), 'x');
+    // Both the current dir and the pre-move one, which a case in use back then still carries.
+    const uploadDir = join(workingDir, '.codeman-uploads');
+    const legacyDir = join(workingDir, '.claude-images');
+    mkdirSync(uploadDir, { recursive: true });
+    mkdirSync(legacyDir, { recursive: true });
+    writeFileSync(join(uploadDir, 'paste-1.png'), 'x');
+    writeFileSync(join(legacyDir, 'paste-0.png'), 'x');
 
     expect((await remove(first)).status).toBe(200);
-    expect(existsSync(join(imageDir, 'paste-1.png'))).toBe(true);
+    expect(existsSync(join(uploadDir, 'paste-1.png'))).toBe(true);
+    expect(existsSync(join(legacyDir, 'paste-0.png'))).toBe(true);
 
     expect((await remove(second)).status).toBe(200);
-    expect(existsSync(imageDir)).toBe(false);
+    expect(existsSync(uploadDir)).toBe(false);
+    expect(existsSync(legacyDir)).toBe(false);
+  });
+
+  it('does not follow a planted symlink at the upload dir into another case when the last session closes', async () => {
+    const other = mkdtempSync(join(tmpdir(), 'codeman-paste-other-'));
+    const otherUploads = join(other, '.codeman-uploads');
+    mkdirSync(otherUploads);
+    writeFileSync(join(otherUploads, 'paste-7.png'), 'x');
+    // Planted by a workspace script. uploadDirs() never lists a link, so the delete
+    // removes nothing here, and the link itself stays: it is not Codeman's to remove.
+    symlinkSync(otherUploads, join(workingDir, '.codeman-uploads'));
+    try {
+      const only = await create();
+      expect((await remove(only)).status).toBe(200);
+      expect(existsSync(join(otherUploads, 'paste-7.png'))).toBe(true);
+      expect(lstatSync(join(workingDir, '.codeman-uploads')).isSymbolicLink()).toBe(true);
+    } finally {
+      rmSync(join(workingDir, '.codeman-uploads'), { force: true });
+      rmSync(other, { recursive: true, force: true });
+    }
   });
 
   it('keeps the images while a sibling is only detached, since it still runs in tmux', async () => {
@@ -154,7 +179,7 @@ describe('deleting a session that shares its working directory', () => {
     // write, so wait for the record a long-running session would already have.
     const store = (server as unknown as { store: { getSession: (id: string) => unknown } }).store;
     await vi.waitFor(() => expect(store.getSession(detached)).toBeTruthy(), { timeout: 10_000 });
-    const imageDir = join(workingDir, '.claude-images');
+    const imageDir = join(workingDir, '.codeman-uploads');
     mkdirSync(imageDir, { recursive: true });
     writeFileSync(join(imageDir, 'paste-2.png'), 'x');
 

test/paste-image-gc.test.ts

@@ -0,0 +1,132 @@
+/**
+ * @fileoverview The hourly upload sweep reads BOTH upload dirs of a live session:
+ * `.codeman-uploads` and the `.claude-images` a case in use before the move still
+ * carries. Only `paste-*` regular files past the age cap go. `uploadDirs()` never
+ * lists a planted symlink, a directory that is, contains or sits inside the data
+ * dir, or anything for a remote session, since the sweep and the delete cleanup
+ * both act on what it returns.
+ */
+import { existsSync, lstatSync, mkdirSync, mkdtempSync, rmSync, symlinkSync, utimesSync, writeFileSync } from 'node:fs';
+import { tmpdir } from 'node:os';
+import { join } from 'node:path';
+import { afterEach, describe, expect, it } from 'vitest';
+import { LEGACY_UPLOADS_DIR, UPLOADS_DIR, sweepPasteImagesOnce, uploadDirs } from '../src/web/paste-image-gc.js';
+
+const DAY_MS = 24 * 60 * 60 * 1000;
+const sessionsOf = (workingDir: string, remote?: unknown) => ({
+  sessions: new Map([['s1', { workingDir, remote } as never]]) as never,
+});
+
+describe('sweepPasteImagesOnce', () => {
+  const dirs: string[] = [];
+  afterEach(() => {
+    for (const dir of dirs.splice(0)) rmSync(dir, { recursive: true, force: true });
+  });
+
+  it('ages paste-* files out of both the current and the legacy upload dir', async () => {
+    const workingDir = mkdtempSync(join(tmpdir(), 'codeman-gc-'));
+    dirs.push(workingDir);
+    const now = Date.now();
+    const current = join(workingDir, UPLOADS_DIR);
+    const legacy = join(workingDir, LEGACY_UPLOADS_DIR);
+    mkdirSync(current);
+    mkdirSync(legacy);
+    expect(uploadDirs({ workingDir })).toEqual([current, legacy]);
+    const old = (now - 8 * DAY_MS) / 1000;
+    const fresh = (now - 1 * DAY_MS) / 1000;
+    const plant = (dir: string, name: string, mtime: number) => {
+      writeFileSync(join(dir, name), 'x');
+      utimesSync(join(dir, name), mtime, mtime);
+    };
+    plant(current, 'paste-1-aa.pdf', old);
+    plant(current, 'paste-2-bb.png', fresh);
+    plant(current, 'keep.png', old); // not an upload of ours
+    plant(legacy, 'paste-0-cc.png', old);
+    symlinkSync(join(legacy, 'paste-0-cc.png'), join(current, 'paste-3-dd.png'));
+    utimesSync(join(current, 'paste-3-dd.png'), old, old);
+
+    const result = await sweepPasteImagesOnce(sessionsOf(workingDir), now);
+
+    expect(result.deleted).toBe(2);
+    expect(existsSync(join(current, 'paste-1-aa.pdf'))).toBe(false);
+    expect(existsSync(join(legacy, 'paste-0-cc.png'))).toBe(false);
+    expect(existsSync(join(current, 'paste-2-bb.png'))).toBe(true);
+    expect(existsSync(join(current, 'keep.png'))).toBe(true);
+    // A planted symlink is skipped (lstat, never followed), so the sweep leaves the link itself.
+    expect(lstatSync(join(current, 'paste-3-dd.png')).isSymbolicLink()).toBe(true);
+  });
+
+  it('never reads through a planted symlink at the upload dir', async () => {
+    const workingDir = mkdtempSync(join(tmpdir(), 'codeman-gc-'));
+    const other = mkdtempSync(join(tmpdir(), 'codeman-gc-other-'));
+    dirs.push(workingDir, other);
+    const now = Date.now();
+    const old = (now - 8 * DAY_MS) / 1000;
+    mkdirSync(join(other, UPLOADS_DIR));
+    writeFileSync(join(other, UPLOADS_DIR, 'paste-9-zz.png'), 'x');
+    utimesSync(join(other, UPLOADS_DIR, 'paste-9-zz.png'), old, old);
+    // readdir follows a link to a directory, so a listed link would let the sweep
+    // age out the other case's uploads through it.
+    symlinkSync(join(other, UPLOADS_DIR), join(workingDir, UPLOADS_DIR));
+
+    expect(uploadDirs({ workingDir })).toEqual([]);
+    expect(await sweepPasteImagesOnce(sessionsOf(workingDir), now)).toEqual({ scanned: 0, deleted: 0 });
+    expect(existsSync(join(other, UPLOADS_DIR, 'paste-9-zz.png'))).toBe(true);
+  });
+});
+
+describe('uploadDirs', () => {
+  const dirs: string[] = [];
+  const savedDataDir = process.env.CODEMAN_DATA_DIR;
+  afterEach(() => {
+    if (savedDataDir === undefined) delete process.env.CODEMAN_DATA_DIR;
+    else process.env.CODEMAN_DATA_DIR = savedDataDir;
+    for (const dir of dirs.splice(0)) rmSync(dir, { recursive: true, force: true });
+  });
+
+  it('lists the upload dir of a home workspace, which sits beside the data dir, not inside it', () => {
+    // The home-as-workspace case the flat name exists for: `<home>/.codeman-uploads`
+    // is a sibling of `<home>/.codeman`, so a prefix test without the separator would
+    // wrongly refuse it.
+    const home = mkdtempSync(join(tmpdir(), 'codeman-gc-home-'));
+    dirs.push(home);
+    process.env.CODEMAN_DATA_DIR = join(home, '.codeman');
+    const dir = join(home, UPLOADS_DIR);
+    mkdirSync(dir);
+    expect(uploadDirs({ workingDir: home })).toEqual([dir]);
+  });
+
+  it('refuses an upload dir that is the data dir, contains it, or sits inside it', () => {
+    const root = mkdtempSync(join(tmpdir(), 'codeman-gc-data-'));
+    const parent = mkdtempSync(join(tmpdir(), 'codeman-gc-link-'));
+    dirs.push(root, parent);
+    const uploads = join(root, UPLOADS_DIR);
+    mkdirSync(join(uploads, 'state'), { recursive: true });
+    // `CODEMAN_INSTANCE=uploads` on a home workspace: the upload dir IS the data dir.
+    process.env.CODEMAN_DATA_DIR = uploads;
+    expect(uploadDirs({ workingDir: root })).toEqual([]);
+    // A data dir pointed inside the upload dir: the recursive delete would take it.
+    process.env.CODEMAN_DATA_DIR = join(uploads, 'state');
+    expect(uploadDirs({ workingDir: root })).toEqual([]);
+    // An upload dir inside the data dir, directly and through a symlinked working
+    // directory (the upload dir itself is real there).
+    process.env.CODEMAN_DATA_DIR = root;
+    expect(uploadDirs({ workingDir: root })).toEqual([]);
+    symlinkSync(root, join(parent, 'ws'));
+    expect(uploadDirs({ workingDir: join(parent, 'ws') })).toEqual([]);
+  });
+
+  it('lists nothing for a remote session, whose workingDir is the remote path', async () => {
+    // The same path on THIS host belongs to whoever has a local case there.
+    const workingDir = mkdtempSync(join(tmpdir(), 'codeman-gc-remote-'));
+    dirs.push(workingDir);
+    mkdirSync(join(workingDir, UPLOADS_DIR));
+    writeFileSync(join(workingDir, UPLOADS_DIR, 'paste-1-aa.png'), 'x');
+    const old = (Date.now() - 8 * DAY_MS) / 1000;
+    utimesSync(join(workingDir, UPLOADS_DIR, 'paste-1-aa.png'), old, old);
+    const remote = { hostId: 'gpu-box' };
+    expect(uploadDirs({ workingDir, remote })).toEqual([]);
+    expect(await sweepPasteImagesOnce(sessionsOf(workingDir, remote))).toEqual({ scanned: 0, deleted: 0 });
+    expect(existsSync(join(workingDir, UPLOADS_DIR, 'paste-1-aa.png'))).toBe(true);
+  });
+});

test/routes/reboot-restore-rebuild-failure.test.ts

@@ -144,7 +144,7 @@ describe('a rebuild that fails after the session is registered', () => {
     expect(ctx.sessions.has('a')).toBe(false);
     // NOT the user-initiated delete: that would bank this session's historical
     // tokens into the lifetime totals, demote a pinned record to `stopped`, and
-    // delete the workspace's .claude-images.
+    // delete the workspace's .codeman-uploads.
     expect(ctx.cleanupSession).not.toHaveBeenCalled();
     await app.close();
   });

test/routes/session-routes.test.ts

@@ -18,9 +18,9 @@ import Fastify, { type FastifyInstance } from 'fastify';
 import fastifyCookie from '@fastify/cookie';
 import fastifyMultipart from '@fastify/multipart';
 import { dirname, join } from 'node:path';
-import { mkdirSync, rmSync, writeFileSync } from 'node:fs';
+import { existsSync, mkdirSync, rmSync, writeFileSync } from 'node:fs';
 import { registryFilePath, reloadCliRegistry } from '../../src/config/cli-registry/registry.js';
-import { mkdtemp, rm, mkdir, writeFile } from 'node:fs/promises';
+import fs, { mkdtemp, rm, mkdir, writeFile, readFile, readdir, symlink } from 'node:fs/promises';
 import { tmpdir } from 'node:os';
 import { createMockRouteContext, type MockRouteContext } from '../mocks/index.js';
 import { installRouteErrorHandler } from '../../src/web/route-error-handler.js';
@@ -285,7 +285,7 @@ describe('session-routes', () => {
       expect(res.statusCode).toBe(200);
       const body = JSON.parse(res.body);
       expect(body.success).toBe(true);
-      expect(body.data.path).toMatch(/\/\.claude-images\/paste-\d+-[a-f0-9]{8}\.jpg$/);
+      expect(body.data.path).toMatch(/\/\.codeman-uploads\/paste-\d+-[a-f0-9]{8}\.jpg$/);
       expect(heicConvert).toHaveBeenCalledWith(heic);
     });
 
@@ -314,10 +314,93 @@ describe('session-routes', () => {
       expect(res.statusCode).toBe(200);
       const body = JSON.parse(res.body);
       expect(body.success).toBe(true);
-      expect(body.data.path).toMatch(/\/\.claude-images\/paste-\d+-[a-f0-9]{8}\.jpg$/);
+      expect(body.data.path).toMatch(/\/\.codeman-uploads\/paste-\d+-[a-f0-9]{8}\.jpg$/);
       expect(heicConvert).toHaveBeenCalledWith(heic);
     });
 
+    const jpeg = Buffer.from('ffd8ffe000104a46494600010100', 'hex');
+    const upload = (name: string, mime: string, bytes: Buffer) =>
+      harness.app.inject({
+        method: 'POST',
+        url: `/api/sessions/${harness.ctx._sessionId}/paste-image`,
+        headers: {
+          host: 'codeman.test',
+          origin: 'http://codeman.test',
+          'content-type': 'multipart/form-data; boundary=codeman-test-boundary',
+        },
+        payload: imageUploadBody('codeman-test-boundary', name, mime, bytes),
+      });
+
+    it('writes into .codeman-uploads with a self-ignoring .gitignore, written once and never over a file already there', async () => {
+      const workDir = await mkdtemp(join(tmpdir(), 'codeman-uploads-'));
+      harness.ctx._session.workingDir = workDir;
+      try {
+        const first = await upload('shot.jpg', 'image/jpeg', jpeg);
+        expect(first.statusCode).toBe(200);
+        expect(JSON.parse(first.body).data.path).toMatch(/\/\.codeman-uploads\/paste-\d+-[a-f0-9]{8}\.jpg$/);
+        expect(await readdir(workDir)).toEqual(['.codeman-uploads']);
+        expect(await readFile(join(workDir, '.codeman-uploads', '.gitignore'), 'utf8')).toBe('*\n');
+
+        await writeFile(join(workDir, '.codeman-uploads', '.gitignore'), 'theirs\n');
+        expect((await upload('shot.jpg', 'image/jpeg', jpeg)).statusCode).toBe(200);
+        expect(await readFile(join(workDir, '.codeman-uploads', '.gitignore'), 'utf8')).toBe('theirs\n');
+      } finally {
+        await rm(workDir, { recursive: true });
+      }
+    });
+
+    it('takes back an ignore file whose write failed, so the next upload writes a real one', async () => {
+      const workDir = await mkdtemp(join(tmpdir(), 'codeman-uploads-'));
+      harness.ctx._session.workingDir = workDir;
+      const ignoreFile = join(workDir, '.codeman-uploads', '.gitignore');
+      // The exclusive create succeeds and the two-byte write fails, as on a full disk.
+      const spy = vi.spyOn(fs, 'writeFile').mockImplementationOnce(async (path) => {
+        await writeFile(path as string, '');
+        throw Object.assign(new Error('no space left on device'), { code: 'ENOSPC' });
+      });
+      try {
+        expect((await upload('shot.jpg', 'image/jpeg', jpeg)).statusCode).toBe(500);
+        expect(existsSync(ignoreFile)).toBe(false);
+        expect((await upload('shot.jpg', 'image/jpeg', jpeg)).statusCode).toBe(200);
+        expect(await readFile(ignoreFile, 'utf8')).toBe('*\n');
+      } finally {
+        spy.mockRestore();
+        await rm(workDir, { recursive: true });
+      }
+    });
+
+    it('refuses a planted symlink at .codeman-uploads and writes nothing through it', async () => {
+      const workDir = await mkdtemp(join(tmpdir(), 'codeman-uploads-'));
+      const elsewhere = await mkdtemp(join(tmpdir(), 'codeman-elsewhere-'));
+      harness.ctx._session.workingDir = workDir;
+      await symlink(elsewhere, join(workDir, '.codeman-uploads'));
+      try {
+        const res = await upload('shot.jpg', 'image/jpeg', jpeg);
+        expect(res.statusCode).toBe(403);
+        expect(JSON.parse(res.body).error).toBe('.codeman-uploads is not a regular directory');
+        expect(await readdir(elsewhere)).toEqual([]);
+      } finally {
+        await rm(workDir, { recursive: true });
+        await rm(elsewhere, { recursive: true });
+      }
+    });
+
+    it('refuses an upload for a remote session before touching disk', async () => {
+      const workDir = await mkdtemp(join(tmpdir(), 'codeman-uploads-'));
+      harness.ctx._session.workingDir = workDir;
+      // A remote session's workingDir is the REMOTE path: a file written here is unreadable there.
+      (harness.ctx._session as unknown as { remote: unknown }).remote = { hostId: 'gpu-box' };
+      try {
+        const res = await upload('shot.jpg', 'image/jpeg', jpeg);
+        expect(res.statusCode).toBe(400);
+        expect(JSON.parse(res.body).error).toMatch(/remote/);
+        expect(await readdir(workDir)).toEqual([]);
+      } finally {
+        (harness.ctx._session as unknown as { remote: unknown }).remote = undefined;
+        await rm(workDir, { recursive: true });
+      }
+    });
+
     it('returns 415 with the error envelope when HEIC conversion fails', async () => {
       heicConvert.mockClear();
       heicConvert.mockRejectedValueOnce(new Error('HEIC dimensions 30000x30000 exceed the 64MP decode limit'));

test/test-ports-guard.test.ts

@@ -52,7 +52,6 @@ const LEGACY_FIXED_PORT_FILES = new Set(
     'operation-lightspeed.test.ts',
     'ownership-scoping.test.ts',
     'pane-exit-sweep.test.ts',
-    'paste-image-dir-shared.test.ts',
     'perf-browser.test.ts',
     'quick-start.test.ts',
     'ralph-integration.test.ts',